Potassium Carbonate → (Z)-3-(4-benzyloxy-2-methyl-phenyl)-2-ethoxy-acrylic acid ethyl ester

HRID 479209Notes

Reaction equation

HRID 479209 reaction equation
[Cl-].[CH2:2]([O:4][CH:5]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH2:36]([O:43][C:44]1[CH:51]=[CH:50][C:47]([CH:48]=O)=[C:46]([CH3:52])[CH:45]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C(O)(C)C>[CH2:9]([O:8][C:6](=[O:7])/[C:5](/[O:4][CH2:2][CH3:3])=[CH:48]/[C:47]1[CH:50]=[CH:51][C:44]([O:43][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:45][C:46]=1[CH3:52])[CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 27598062-Methyl 4-benzyloxybenzaldehydeHCID 11327835Phosphonium, (1,2-diethoxy-2-oxoethyl)triphenyl-, chloride (1:1)3×

Product 1

HCID 68617018(Z)-3-(4-benzyloxy-2-methyl-phenyl)-2-ethoxy-acrylic acid ethyl esterYield 60%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

(Ethoxy-ethoxycarbonyl-methyl)-triphenyl-phosphonium chloride (3.79 g, 8.8 mmol) and potassium carbonate (1.46 g, 10.6 mmol) were added to a solution of 4-benzyloxy-2-methyl-benzaldehyde (0.8 g, 3.5 mmol) in isopropanol (10 ml) at 10° C. under an argon atmosphere [for the preparation of (ethoxy-ethoxycarbonyl-methyl)-triphenyl-phosphonium chloride see: K. K. Bach, H. R. El-Seedi, H. M. Jensen, H. B. Nielsen, I. Thomson, K. B. G. Torssell, Tetrahedron 1994, 50, 7543-7556]. The suspension was heated to 60° C. After 12 h and after 20 h (ethoxy-ethoxycarbonyl-methyl)-triphenyl-phosphonium chloride (each time 3.79 g, 8.8 mmol) and potassium carbonate (each time 1.46 g, 10.6 mmol) were added again. After 36 h the suspension was filtered off and the filtrate was evaporated under reduced pressure. The residue was dissolved in dichloromethane, washed with saturated aqueous ammonium chloride and ice water and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, dichloromethane) to give 0.7 g (2.1 mmol, 58%) of the title compound as yellow liquid.

Workup

  1. filtrationAfter 36 h the suspension was filtered off
  2. customthe filtrate was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with saturated aqueous ammonium chloride and ice water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue purified by column chromatography (silica gel, dichloromethane)

Sources & evidence

ORD record
ord-97199bd2b93641ba9ba3bddf38e9bdee
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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